Solving Multiple Daddy Issues

(My best friend at work recently found out his father is in very poor health and doesn’t have much time left. He’s been processing the news and figuring out how to approach the situation; they haven’t seen each other in years and live about a thousand miles apart. He’s also been the type to always look out for himself; he doesn’t like having to rely on anyone else. We don’t have the same positions at our workplace. I make more than him as well as having a second job that tires me out, but pays an almost embarrassing amount for the hours I put in.)

Me: “I’m not trying to tell you what to do because I can’t do that, and also nobody can because you’re a grown man and stubborn as hell but… You should go see your dad.”

Friend: “I know… I don’t have much time off banked, though.”

Me: “Yeah… I know you’d talked to [Manager] about what’s going on, so I may have asked if we can transfer or donate PTO like at some workplaces, because I have a ton and never use it. There isn’t a way to do that, but he said if you ask he can put in a couple fake training days for you to help you cover.” *meaning: submit paperwork so the company pays him like he went to school even though he didn’t*

Friend: “Wow, that’s really cool of him. I still don’t know if I’d be able to swing it, though. It’s a lot of money.”

Me: “Don’t let that stop you; I’ll cover whatever you need. You’ll regret it forever if you don’t go and I don’t want that for you. Just let me know.”

Friend: “Oh, sweetheart. I really appreciate that, but we both know I won’t take you up on it. I gotta have my pride. I’ll figure something out; I always do.”

Me: “Of course. But hon, we ALSO both know I get paid a STUPID amount of money.”

Friend: *laughs* “Yeah, you do.”

Me: “So I gotta put it out there. Just in case.”

(He’s started planning the trip.)